Island Hopper Songwriter Festival returns this weekend to Fort Myers Beach
Fort Myers Beach is ready to turn into South Nashville this weekend as the Island Hopper Songwriter Festival rolls into town Friday with dozens of musical performances featuring Nashville and local artists slated for Fort Myers Beach restaurants and bars, culminating in the festival finale at the Pink Shell Beach Resort pool party this Sunday.
The festival is showcasing more than 60 performers from Nashville, including Grammy Award-nominated songwriters and chart-topping artists. The festival started in Captiva last Friday and is making its way through Cape Coral and Fort Myers throughout the week before reaching Fort Myers Beach on Friday.
The Pink Shell Beach Resort and Marina pool party headliner this year will be country singer Michael Ray, who is known for the country hit “Kiss You in the Morning.” Doors for the sold-out show open at 4:30 p.m. The concert begins at 5:30 p.m.
“We look forward to hosting the 11th annual Island Hopper Grand Finale Pool Party featuring Michael Ray and celebrating some of the incredible artists who have graced our stage over the years, including Maren Morris, Gary LeVox, Chris Young, and Rodney Atkins, to name a few,” Pink Shell Beach Resort & Marina General Manager Bill Waichulis said. “Our team eagerly anticipates this event each year, as it is a fantastic opportunity to create unforgettable experiences for our guests, owners, and the local community. We are proud to be part of an event that brings people together through great music, great memories, and the vibrant spirit of Southwest Florida.”
For those that can’t grab tickets for the pool party and still want to enjoy some first-class country entertainment on Fort Myers Beach, there will be a slew of venues and options throughout that day and the rest of the weekend for that matter offering up mostly-free performances as part of the Island Hopper Songwriter’s Festival.
Participating Fort Myers Beach venues include Bayside Veteran’s Park, Diamondhead Beach Resort, Lighthouse Island Resort, Margaritaville Beach Resort, On the Bay, The Whale, and the Yucatan Beach Stand Bar & Grill.
Fort Myers Beach will include three ticketed events. In addition to the Pink Shell pool party, there will be a “Music on the Mound” performance on Saturday, Sept. 26 featuring Frank Myers and Lauren Mascitti at the Mound House on Connecticut Street. Myers is known for co-writing the megahit “I Swear,” which was recorded by John Michael Montgomery, and All-4-One. Mascitti’s album “God Made a Woman” reached #4 on the iTune country albums chart.
On that same day, the festival will hold a new ticketed event for Fort Myers Beach with the Sunset Songwriter Cruise out of Fort Myers Beach aboard Adventures in Paradise featuring singer/songwriter Robinson Treacher. “He has a great voice, great talent,” Lee County Visitor & Convention Bureau communications manager Miriam Dotson said. The bureau is one of the organizers of the event.
While tickets must be purchased for those shows, there will be a plethora of free music performances on Fort Myers Beach this weekend.
On Friday, the festival will begin on Fort Myers Beach at the Margaritaville Beach Resort at 4 p.m., where seven artists will be performing.
Starting at 7 p.m., there will be musical performances occurring simultaneously at Bayside Veteran’s Park, the Diamondhead Beach Resort, Lighthouse Island Resort, On the Bay, Pink Shell Beach Resort, and the Yucatan Beach Stand Bar & Grill. The songs will continue to roll throughout the night, with another round of performances scheduled to begin at 8:30 p.m.
A number of the performers will be switching between venues throughout the weekend.
Beginning at 7:30 p.m. on Friday at Margaritaville will be Katrina Cain, Taylor Hughes, Kelly Neff, Matt McKinney, Race Ricketts, Ry Rivers, and Kurt Stevens. Neff will then perform at DiamondHead Beach Resort at 7 p.m., along with Elisabeth Ann. Elisabeth Ann is a Nashville-based artist originally from Illinois who began her career performing in Fort Myers.
Brian Sutherland, a Fort Myers native who has toured with The Beach Boys, will be playing the Lighthouse Resort at 7 p.m. on Friday, and then will cap off Saturday night’s showcase at the DiamondHead Beach Resort at 10 p.m.
Myers, who is also known for co-writing Lonestar’s No. 1 hit “I’m Already There,” will be giving a free performance at the Diamondhead Beach Resort on Friday night at 8:30 p.m. Myers will give another free show at Bayside Veteran’s Park on Sunday at 3:30 p.m.
Bayside Veteran’s Park will have four free performances on Friday night. Located between Nervous Nellie’s and Snug Harbor Waterfront Restaurant, off Old San Carlos Boulevard on Fort Myers Beach, the venue will host Nashville artists Katie Lyon and Ava Suppelsa on Friday beginning at 7:15 p.m. Suppelsa co-wrote Max McNown’s platinum single “Better Me For You (Brown Eyes).”
Suppelsa, whose songs have also been record by Lady A, Carly Pearce, Max McNown, and Keith Urban, can also be seen at On the Bay on Saturday at 4:15 p.m. She will play Margaritaville on Saturday at 8 p.m. and on Sunday at 8 p.m.
On Saturday at Bayside Veteran’s Park, Nelson Cade and Tim McGeary will perform free shows beginning at 4:15 p.m., followed by Lauren Mascitti and Bobby Tomberlin at 6:45 p.m. Tomberlin is an acclaimed country artist who was nominated for a Grammy Award for co-writing the Dolly Parton/Bill Anderson single “Someday It’ll All Make Sense.”
Tomberlin has also written songs recorded by Barbra Streisand, Faith Hill, Blake Shelton, Uncle Kracker, Josh Turner, Kenny Rogers, Joe Nichols, Vince Gill, Rodney Atkins, Pam Tillis, Jerry Lee Lewis and others His latest release, “Out Of Road,” featured guest vocals by Vince Gill, Bill Anderson and Bobby Bare.
In addition to playing Bayside Veteran’s Park on Saturday, Tomberlin will also play Bayside Veteran’s Park on Sunday with Myers for a concert set to start at 3:30 p.m. Tomberlin can be also seen at On the Bay at 7 p.m. on Friday, and the Lighthouse Island Resort on Saturday at 2:45 p.m.
The music on Saturday at the DiamondHead Beach Resort will begin at 4 p.m. with performances by Nate Bass and Madison Morris. Morris is a three-time Grammy-submitted singer-songwriter whose work has appeared on the official Grammy consideration ballots in 2023 (“We’re All Still Here”), 2024 (“Hard Rain”), and 2025 (“Eve of Revolution”), with “Hard Rain” also earning a 2025 Josie Award nomination for Americana Song of the Year. They will be followed on stage by Lyon and Neff at 6:30 p.m., and then McKinney and Rivers at 8 p.m.
While most of the shows at the festival do not require a ticket and are free, other ticketed events on the festival this week include the new “Stars on the River” concert with LOCASH and Alexandra Kay at Caloosa Sound Amphitheater on Wednesday in Fort Myers.
The Island Hopper Songwriter Fest is presented by BMI, iHeartRadio’s Cat Country 107.1, Florida Restaurant & Lodging Association and Lee the County Visitor & Convention Bureau.
The Lee County Visitor & Convention Bureau is involved in organizing the event in conjunction with BMI and iHeartRadio in a process that Dotson said involves “yearlong preparation.” the organization was excited about the addition of new venues this year, including the Caloosa Amphitheatre in Fort Myers, and the songwriter cruise on Fort Myers Beach.
“We are looking to get visitors to get to the restaurants, and drive some business,” Dotson said.
Other ticketed events during the week include:
Sept. 24: Luminary’s Dinner Experience with Nate Bass of British brother trio Essex County at Luminary Hotel & Co.’s culinary theater in downtown Fort Myers.
Sept. 24: ACMA Showcase with Roy Schneider, Anthony Wayne, Bill Metts, Tim McGeary and Matt Hannam at Sidney & Berne Davis Art Center in downtown Fort Myers.
For the full lineup, schedule and ticket information, visit Islandhopperfest.com.